Sodium Hydroxide → (S)-2-(2,4-difluorophenyl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylic acid

HRID 1403574Notes

Reaction equation

HRID 1403574 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][C@@H:20]2[CH3:25])=[N:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:26]([O:28]C)=[O:27])[CH:15]=2)[N:10]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][C@@H:20]2[CH3:25])=[N:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:26]([OH:28])=[O:27])[CH:15]=2)[N:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70665077(S)-methyl 2-(2,4-difluorophenyl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylate

Product 1

HCID 70665149(S)-2-(2,4-difluorophenyl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylic acidYield 57.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of (S)-methyl 2-(2,4-difluorophenyl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylate (100 mg, 0.25 mmol) in methanol (30 mL) and water (1.0 mL) was added sodium hydroxide (40 mg, 1.00 mmol) with stirring overnight at room temperature. The reaction mixture was concentrated in vacuo, dissolved in water (10 mL) and adjusted to pH 5 with HCl (3N). The solids were collected by filtration to afford (S)-2-(2,4-difluorophenyl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylic acid as a light yellow solid (55.5 mg, 57.5%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in water (10 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-4ae6213a6c6f4a709cd35fe5170b0f5b
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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